PT87828B - Processo para a preparacao de herbicidas do tipo sulfonilureia e de composicoes herbicidas que os contem - Google Patents
Processo para a preparacao de herbicidas do tipo sulfonilureia e de composicoes herbicidas que os contem Download PDFInfo
- Publication number
- PT87828B PT87828B PT87828A PT8782888A PT87828B PT 87828 B PT87828 B PT 87828B PT 87828 A PT87828 A PT 87828A PT 8782888 A PT8782888 A PT 8782888A PT 87828 B PT87828 B PT 87828B
- Authority
- PT
- Portugal
- Prior art keywords
- radical
- general formula
- alkyl
- optionally substituted
- halogen atoms
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims abstract description 7
- 239000000203 mixture Substances 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 methoxymethoxy Chemical group 0.000 claims abstract description 31
- 125000005843 halogen group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000005005 aminopyrimidines Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
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- 239000000654 additive Substances 0.000 description 4
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
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- 238000005056 compaction Methods 0.000 description 2
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- 239000011368 organic material Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8709177A FR2617167B1 (fr) | 1987-06-25 | 1987-06-25 | Herbicides de type sulfonyluree, leur preparation, les compositions les contenant et leur utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT87828A PT87828A (pt) | 1989-05-31 |
| PT87828B true PT87828B (pt) | 1992-10-30 |
Family
ID=9352654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT87828A PT87828B (pt) | 1987-06-25 | 1988-06-24 | Processo para a preparacao de herbicidas do tipo sulfonilureia e de composicoes herbicidas que os contem |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4960454A (xx) |
| JP (1) | JPS6426584A (xx) |
| KR (1) | KR890000468A (xx) |
| CN (1) | CN1022016C (xx) |
| AR (1) | AR243896A1 (xx) |
| BR (1) | BR8803264A (xx) |
| DD (1) | DD271259A5 (xx) |
| DK (1) | DK348388A (xx) |
| EG (1) | EG18638A (xx) |
| FI (1) | FI88507C (xx) |
| FR (1) | FR2617167B1 (xx) |
| HU (1) | HU202874B (xx) |
| IL (1) | IL86800A0 (xx) |
| MA (1) | MA21306A1 (xx) |
| MX (1) | MX12003A (xx) |
| OA (1) | OA08883A (xx) |
| PT (1) | PT87828B (xx) |
| TR (1) | TR24147A (xx) |
| ZA (1) | ZA884558B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0514768T3 (xx) * | 1991-05-18 | 1997-02-17 | Hoechst Schering Agrevo Gmbh | |
| CN103484531B (zh) * | 2005-07-01 | 2015-10-21 | 巴斯福股份公司 | 抗除草剂的向日葵植物、编码抗除草剂的乙酰羟酸合酶大亚基蛋白的多核苷酸和使用方法 |
| US20110201578A1 (en) * | 2010-02-14 | 2011-08-18 | Nyangenya Maniga | Composition and methods for the treatment of pseudofolliculitis barbae and skin irritation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| DE2862234D1 (en) * | 1978-11-01 | 1983-05-19 | Du Pont | Herbicidal sulfonamides, their preparation, compositions containing them and use thereof |
| JPS57146764A (en) * | 1981-01-26 | 1982-09-10 | Du Pont | Sulfonyl urea n oxides |
| DK536582A (da) * | 1981-12-07 | 1983-06-08 | Du Pont | Herbicide sulfonamider |
| US4534790A (en) * | 1982-10-07 | 1985-08-13 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ATE35888T1 (de) * | 1983-03-28 | 1988-08-15 | Ciba Geigy Ag | N-phenylsulfonyl-n'-pyrimidinyl- und triazinylharnstoffe. |
| US4878937A (en) * | 1985-05-14 | 1989-11-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4786734A (en) * | 1986-11-28 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal pyridine sulfonamides |
-
1987
- 1987-06-25 FR FR8709177A patent/FR2617167B1/fr not_active Expired
-
1988
- 1988-06-15 US US07/206,740 patent/US4960454A/en not_active Expired - Fee Related
- 1988-06-20 IL IL86800A patent/IL86800A0/xx unknown
- 1988-06-22 MX MX1200388A patent/MX12003A/es unknown
- 1988-06-22 MA MA21549A patent/MA21306A1/fr unknown
- 1988-06-23 EG EG353/88A patent/EG18638A/xx active
- 1988-06-23 FI FI883031A patent/FI88507C/fi not_active IP Right Cessation
- 1988-06-23 AR AR88311202A patent/AR243896A1/es active
- 1988-06-23 JP JP63155987A patent/JPS6426584A/ja active Pending
- 1988-06-24 TR TR88/0453A patent/TR24147A/xx unknown
- 1988-06-24 HU HU883219A patent/HU202874B/hu not_active IP Right Cessation
- 1988-06-24 DD DD88317124A patent/DD271259A5/de not_active IP Right Cessation
- 1988-06-24 DK DK348388A patent/DK348388A/da not_active Application Discontinuation
- 1988-06-24 CN CN88103930A patent/CN1022016C/zh not_active Expired - Fee Related
- 1988-06-24 PT PT87828A patent/PT87828B/pt not_active IP Right Cessation
- 1988-06-24 OA OA59377A patent/OA08883A/xx unknown
- 1988-06-24 ZA ZA884558A patent/ZA884558B/xx unknown
- 1988-06-25 KR KR1019880007740A patent/KR890000468A/ko not_active Application Discontinuation
- 1988-06-27 BR BR8803264A patent/BR8803264A/pt not_active Application Discontinuation
-
1990
- 1990-06-22 US US07/541,940 patent/US5096484A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1030080A (zh) | 1989-01-04 |
| DK348388A (da) | 1988-12-27 |
| ZA884558B (en) | 1989-03-29 |
| MA21306A1 (fr) | 1988-12-31 |
| US4960454A (en) | 1990-10-02 |
| FI88507B (fi) | 1993-02-15 |
| DK348388D0 (da) | 1988-06-24 |
| EG18638A (en) | 1993-08-30 |
| PT87828A (pt) | 1989-05-31 |
| BR8803264A (pt) | 1989-01-31 |
| JPS6426584A (en) | 1989-01-27 |
| FR2617167A1 (fr) | 1988-12-30 |
| FI883031A (fi) | 1988-12-26 |
| FI88507C (fi) | 1993-05-25 |
| AR243896A1 (es) | 1993-09-30 |
| IL86800A0 (en) | 1988-11-30 |
| FI883031A0 (fi) | 1988-06-23 |
| HU202874B (en) | 1991-04-29 |
| FR2617167B1 (fr) | 1989-11-24 |
| DD271259A5 (de) | 1989-08-30 |
| HUT49618A (en) | 1989-10-30 |
| MX12003A (es) | 1993-09-01 |
| CN1022016C (zh) | 1993-09-08 |
| TR24147A (tr) | 1991-04-25 |
| OA08883A (fr) | 1989-10-31 |
| KR890000468A (ko) | 1989-03-14 |
| US5096484A (en) | 1992-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG3A | Patent granted, date of granting |
Effective date: 19920427 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19941031 |